Ammonium Chloride → 1-(2'-(Benzyloxy)-3'-tert-butylbiphenyl-3-yl)-1-(2-methoxyphenyl)ethanol

HRID 45474

Reaktionsgleichung

Reaktionsgleichung von HRID 45474
[CH2:1]([O:8][C:9]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25](=[O:27])[CH3:26])[CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[Mg]Br.[Cl-].[NH4+]>O1CCCC1>[CH2:1]([O:8][C:9]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[O:29][CH3:28])([OH:27])[CH3:26])[CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 582385981-(2'-(Benzyloxy)-3'-tert-butylbiphenyl-3-yl)ethanoneHCID 178489560HCID 178489560, Verbindung

Produkt 1

HCID 582385991-(2'-(Benzyloxy)-3'-tert-butylbiphenyl-3-yl)-1-(2-methoxyphenyl)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 36 (0.8 g, 2.23 mmol) in anhydrous tetrahydrofuran (8 mL) was stirred under nitrogen at room temperature and 1M ortho-methoxyphenyl magnesium bromide in tetrahydrofuran (3 mL, 1.35 equiv.) was slowly added. Stirring was continued at room temperature for 30 min and at 60° C. for 3 hr. After cooling, the reaction mixture was poured on saturated ammonium chloride (120 mL) and extracted with ethyl acetate (150 mL). The organic extract was washed with water (2×50 mL), dried over sodium sulfate and filtered. The solvent was removed in a rotary evaporator and the crude 37 thus obtained was used in the next step without further purification.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate (150 mL)
  3. extractionThe organic extract
  4. washwas washed with water (2×50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed in a rotary evaporator
  8. customthe crude 37 thus obtained
  9. customwas used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-d0dbe5b4edf345aa848c9fad3f26678e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541522B2

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